Water → HCID 17964443, compound

HRID 1814430Notes

Reaction equation

HRID 1814430 reaction equation
[C:1]1(=[O:30])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.C[Sn]([N:35]=[N+:36]=[N-:37])(C)C.[C:38]1([C:44](Cl)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>C1(C)C(C)=CC=CC=1>[C:4]1(=[O:25])[N:5]([CH2:6][CH2:7][CH2:8][N:9]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:11][CH2:12][C:13]2[N:35]([C:44]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:36]=[N:37][N:14]=2)[C:1](=[O:30])[C:2]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:3]12

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 5104973Azido(trimethyl)stannaneHCID 69529877HCID 69529877, compound

Product 1

HCID 17964443HCID 17964443, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 4-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butyronitrile (336 mg, 0.84 mmol) in xylene (5 ml) was added trimethyltin azide (378 mg, 1.84 mmol). The mixture was stirrred at 115° C. for 18 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was dissolved with 17% THF/CH2Cl2 (2.4 ml). To the solution was added 10 N NAOH solution (107 μl, 1.07 mmol). After srirring at RT for 30 min, triphenylmethyl chloride (297 mg, 1.07 mmol) was added, and the mixture was stirred at RT for 7 h, After adding water, the mixture was extracted with chloroform, washed with brine, dried over sodium sulfate, and filtered. Concentrating under vacuum gave 3-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro 1-naphthyl)amino]-1-[1-(triphenylmethyl)tetrazol-5-yl]propane (125 mg, 22%) which was used in the next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum to dryness
  3. dissolutionthe residue was dissolved with 17% THF/CH2Cl2 (2.4 ml)
  4. waitAfter srirring at RT for 30 min
  5. extractionthe mixture was extracted with chloroform
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationConcentrating under vacuum

Sources & evidence

ORD record
ord-9a9722b2f6e84662bd95b5150eedcfba
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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